Tetrahydrofuran → 1-[2-(Trimethylsilyl)ethylcarbonyl]-4-(4-nitrophenyl)piperazine
반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)O[CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21].[O:35]1CCC[CH2:36]1>>[CH3:23][Si:20]([CH3:21])([CH3:22])[CH2:19][CH2:18][C:36]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1)=[O:35]참가 물질
4
실험 절차
A solution of 1-(4-nitrophenyl)piperazine (10 g, 48.31 mmol) and 2-(trimethylsilyl)ethyl p-nitrophenyl carbonate (14.4 g, 50.73 mmol) in tetrahydrofuran (220 mL) is refluxed for 3 hours with magnetic stirring and then stirred for 20 hours at room temperature. The reaction mixture is concentrated, the residue is taken up in dichloromethane and the organic phase is washed 4 times with 1N sodium hydroxide and twice with water. The organic phase is then dried over sodium sulphate, filtered and concentrated; the oily residue obtained is used without further purification in the following step (12 g, yield: 71%). 1H NMR (300 MHz, δ ppm) CDCl3: 0.04 (s, 9H), 1.02 (m, 2H), 3.43 (m, 4H), 3.65 (m, 4H), 4.22 (m, 2H), 6.82 (d, 2H), 8.13 (d, 2H).
후처리
- stirringstirred for 20 hours at room temperature
- concentrationThe reaction mixture is concentrated
- washthe organic phase is washed 4 times with 1N sodium hydroxide
- dry with materialThe organic phase is then dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customthe oily residue obtained
- customis used without further purification in the following step (12 g, yield: 71%)
출처 및 근거
- ORD 기록
- ord-6f99f1947b24468884407db31391d5b9
- 출처 데이터셋
- uspto-grants-2004_09
- 특허 번호
- US06794382B2
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